I too have wanted to make this trip. I was wondering if you ever made it happen? Any input or advice, would love to hear about the trip. Have a great day!
We sail the Upper Keys frequently and I can give you the following advice without knowing mast height or draft:
Snake creek bridge
In our previous 50’ boat we sailed from Miami during the day and overnight downwind straight through to the park. Boca Grande is a good stop if you want to break up the trip.
Our 3 favorite stops on the inside route are:
Anchor off the Marriott & Dinner at Sundowners Blackwater sound
Cowpens bay & dinner at Marker 88
Be sure to dive at Loggerhrad Key
Let me know if you have any questions